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G0259

Sigma-Aldrich

D-Glucosaminic acid

≥98% (TLC)

Synonym(s):

2-Amino-2-deoxy-D-gluconic acid

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About This Item

Empirical Formula (Hill Notation):
C6H13NO6
CAS Number:
3646-68-2
Molecular Weight:
195.17
Beilstein:
1726033
EC Number:
222-879-1
MDL number:
MFCD00037764
UNSPSC Code:
12352201
PubChem Substance ID:
24895011
NACRES:
NA.25

Quality Level

100

Assay

≥98% (TLC)

form

powder

optical activity

[α]20/D -15.0 to -14.0 °, c = 2.5% (w/v) in hydrochloric acid

technique(s)

thin layer chromatography (TLC): suitable

color

white to off-white

mp

235 °C

solubility

0.5 M HCl: 50 mg/mL, clear, colorless to faintly yellow

storage temp.

2-8°C

SMILES string

N[C@H]([C@@H](O)[C@H](O)[C@H](O)CO)C(O)=O

InChI

1S/C6H13NO6/c7-3(6(12)13)5(11)4(10)2(9)1-8/h2-5,8-11H,1,7H2,(H,12,13)/t2-,3-,4-,5-/m1/s1

InChI key

UFYKDFXCZBTLOO-TXICZTDVSA-N

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Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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D Horton et al.
Carbohydrate research, 193, 49-60 (1989-10-31)
Acetylation of 2-amino-2-deoxy-D-gluconic acid (1) with acetyl chloride-pyridine gave 2,3-unsaturated six- and five-membered lactones (2 and 3). Their benzoylated analogs (4 and 5) were obtained by benzoylation of 1 with benzoyl chloride-pyridine. Reaction of 1 with hot acetic anhydride-sodium acetate
N-methyl-1-glucosaminic acid.
M L WOLFROM et al.
Journal of the American Chemical Society, 68(11), 2343-2345 (1946-11-01)
Beata Liberek et al.
Carbohydrate research, 340(11), 1876-1884 (2005-06-28)
Mono- and di-N-alkylated derivatives of 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-beta-D-glucose (alkyl=methyl, ethyl, propyl, butyl, pentyl, hexyl, benzyl) were synthesised by the reductive alkylation of per-O-acetyl-d-glucosamine. (N-ethyl, N-propyl, N-butyl, N-pentyl and N-hexyl)-1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-beta-D-glucoses were deacetylated in order to attempt an enzymatic phosphorylation. All products were characterised
E T Zavras et al.
The Journal of parasitology, 70(6), 937-944 (1984-12-01)
It was shown previously that worm-conditioned saline (WCS) prepared from crowded 10-day-old H. diminuta inhibited the incorporation of 3H-thymidine into DNA in the anterior regions of uncrowded worms and that the inhibition was partially accounted for by succinate and acetate
Fabio Pezzotti et al.
Carbohydrate research, 340(1), 139-141 (2004-12-29)
D-glucosaminic acid (2-amino-2-deoxy-D-gluconic acid), a component of bacterial lipopolysaccharides and a chiral synthon, is easily prepared on a multigram scale by air oxidation of D-glucosamine (2-amino-2-deoxy-D-glucose) catalysed by glucose oxidase.
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